


The Date Doctor

by Jurrassica



Category: Compilation of Final Fantasy VII, Crisis Core: Final Fantasy VII, Final Fantasy VII Remake (Video Game 2020)
Genre: Alternate Universe - Modern Setting, Awkward Dates, Cliche, Cloud hates love, Crushes, Eventual Smut, F/M, Falling In Love, Gossip, M/M, New York City, Romantic Comedy, Zack and Wedge are bro's, Zack is awkward, Zack is smooth, clumsy love
Language: English
Status: In-Progress
Published: 2020-09-25
Updated: 2020-11-24
Packaged: 2021-03-08 04:15:05
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 11,509
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/26639407
Author URL: https://archiveofourown.org/users/Jurrassica/pseuds/Jurrassica
Summary: Smooth-talking Zack Fair is a professional "date doctor". He coaches his clients on how to woo their love interests, with the focus on having long-term, happy relationships. But when Zack meets Cloud Strife, a journalist for a popular gossip website, everything he has ever known to work in romance suddenly fails him. And he finds himself making a complete fool out of himself.
Relationships: Minor or Background Relationship(s), Wedge/Jessie, Zack Fair/Cloud Strife
Comments: 32
Kudos: 67





	1. Dating 101

**Author's Note:**

  * For [blindinglights](https://archiveofourown.org/users/blindinglights/gifts).



> This is based on a movie from 2005 called "Hitch"! I'm not normally into romcoms, but I love this movie! 
> 
> Now I know the movie Hitch doesn't have sex in it, but this is fanfiction about Zack and Cloud, so there will be smut in the last chapter (chapter 4). Also, Tifa and Cloud are step-siblings in this, and call each other brother and sister
> 
> Also, I wanna gift this to Bindinglights cause she's wanted to read this for a while. So here you go, buddy :)

No one wakes up thinking; ‘I hope I don’t meet the person of my dreams today’. A lot of people also won’t just go looking for love. Instead, they’ll say ' _I'm too into my career_ ' or ' _I'd rather be friends_ ' or even ' _I'm not looking for a relationship right now_ '. What they really mean is 'Leave me the fuck alone' or ' _Try harder, moron_ '. The hard part is finding out which one they mean. Yeah, they’re going to lie to you, to spar your feelings. They don’t even know you yet, so can you really blame them? Not yet at least. That's where I come in. I'll help you figure it out. That’s my job, and I do it well.

You need to be yourself. _Please_ be yourself and don’t put on a front. I can’t tell you how many messed up dates I’ve seen because someone tries too hard to be something they’re not. Your date will know, and it’ll make my job a lot harder. Don’t act shy if you’re not shy, and don’t act outgoing if you’re not outgoing. Just remember, they’re already out with you, right? They already said yes. That’s the hardest part, and you’ve passed that hurdle.

Make sure you listen and respond. Ask how they liked the movie, what painting they liked, and how their food was. Don’t look at their mouth, or chest, or wonder what they look like naked. Focus on _them_. The emotional part is just as important as the sexual part. And intimacy can be both.

So what _does_ true love look like? No one really knows. But it happens in the blink of an eye. One moment, you’re enjoying your life, and the next you’re wondering how you ever lived without them.

Three dates is all I need, and after that, you’re golden. The third date is typically where the magic happens. The first kiss. Most people believe the first kiss will show anyone what they need to know about the relationship. After that? Well, you’re on your own, I’ll be out of the picture completely. I helped you out as best I could. 

Life isn’t the amount of breaths you take. It’s the moments that take your breath away.

Corny? I know, but I promise, people love corny. They just won’t admit it.

* * *

“Cloud! Oh my, you’re back already? Aren’t you supposed to come back next week?” Andrea Rhodea greeted, a shocked look on his face the moment his eyes fell on Cloud as he walked into their office. He swore Cloud wasn’t supposed to be back for a few more days. After the weekend, at least.

“I have something that was too good to hold on to.” Cloud replied with a shrug, clearly not affected or concerned that he was coming to work when he was technically still on vacation. Didn’t matter, Cloud liked his job enough to come by on his days off. That, and he was the top reporter for all the delicious celebrity drama that everyone ate up nowadays.

“Yeah? And what could you have possibly seen on the beautiful beaches of the Bahamas? A man, perhaps?” Andrea pressed. Always pressing, always changing the subject to turn it into him finding a man. Drove Cloud crazy, how much his coworkers, friends, and sister just _loved_ to butt into his life.

“No. You already know I went alone.” Cloud rolled his eyes, hating that one of the first things out of his coworkers mouth had to do with meeting a man. Really, couldn’t people just be happy being single nowadays?

“You went alone...to where couples go, or where people hook up, but you didn’t hook up. Aren’t you lonely, Cloud?”

“Why would I be lonely?” Cloud asked. He actually _enjoyed_ going to places alone. He could clear his mind, read, and just relax without other people breathing down his neck. “I have my sister and Aerith. Who else do I need?”

“A boyfriend?”

“No, Andrea. not a boyfriend.” Cloud was starting to feel irritation clawing at the back of his neck, the small hairs standing up. “Relationships are just for people waiting for something better to come along. I’m happy where I am. I enjoy my job, and my solo vacations just fine. I don’t need or want a man to interfere with any of that.”

“Cloud, dude,” Kunsel called out, brow raised in concern, interrupting the little talk between them. “What are you doing here?”

“I work here, remember? Or did you already forget about me?” Cloud asked, arms folded at his chest, like he was daring Kunsel to kick him out.

“Yes, but not until Monday. Go home. Go to the bar and find some guy to hook up with or something. ‘Cause I can bet you didn’t do that during your vacation.” Kunsel shook his head, turning heel towards his office. Cloud rolled his eyes. Yeah, even his own boss was always pushing him to hook up with someone. Why was everyone so invested and interested in his sex and love life?

“I have some pictures that you’d find more than interesting.” Cloud replied, stopping Kunsel in his tracks. Cloud always did have the best gossip, and Kunsel knew it. Kunsel always asked him, too, how he found everything out, but Cloud would never give away his secrets.

“Not today, Cloud. Go home and enjoy the rest of your vacation. Tell me Monday. I’m sure it can wait.” Kunsel started walking again, totally intending to ignore Cloud until he went away.

“I saw Genesis making out with some guy on the beach while I was on vacation. That’s not interesting enough for you?” Genesis was a Broadway actor, most famously known for the play ‘Loveless’. The man that Cloud had seen him with, was most certainly a _nobody_. It was rumored that Genesis was dating someone, in secret, for a while now. But there had never been even a sliver of proof. No one ever saw Genesis with anyone that would even remotely resemble a lover. Now word would be out about the handsome raven he was seen with on the beaches of the Bahamas.

“Oh? Well, come to my office then.” Kunsel was a sucker for any gossip that involved celebrities that tended to stay under the radar. 

Really, Cloud Strife loved his job. Working as a writer for one of the largest pop culture gossip sites on the internet had its perks. He was able to afford a quaint little apartment on the upper east side, as well as afford a vacation or two per year. Honestly. He couldn’t ask for anything better. Going to college for journalism was probably the best idea he ever had. 

It also helped that people loved juicy and dramatic gossip about celebrities. People drank that shit up, and Cloud knew how to find the best gossip.

And his boss seemed to always like his work. So that was a plus.

“These are great, Cloud!. Type up the column for me, and email it. But do it first thing Monday. I don't want to see your face until then. Go enjoy the rest of your vacation."

* * *

“And how’d you meet him?” Cloud asked, sitting back on the lounge chair. He and his best friend, Aerith, had met at their favorite bar. Something they did often, and whenever they had news to share with one another. In this case, it was about Aerith meeting someone, and Cloud telling her about his vacation.

“Oh! Well, I was at Victoria’s Secret, I needed some new bras He was buying pajamas for his mother-”

“Aerith.” Cloud warned. “There’s no way he was buying pajamas for his mother. He was buying lingerie for another woman. Which means that he was hitting on you while buying something for another woman.”

“Come on Cloud.” Aerith whined, hitting him playfully on the shoulder. Sometimes she hated how negative he could be.

“Not all men are trash, you know that, right?” Cloud rolled his eyes at the mere thought, sipping his drink.

“What’s his name?” He asked, curious. 

“Why? So you can use your magic detective powers to find out _way_ too much about this guy? I’m on to you, silly!” Aerith jokes. Really, this was all fine. Aerith was his best friend, and he enjoyed spending time with her. Same went for his sister, Tifa (and her husband). He didn’t need a man in his life. His life was already perfect. A boyfriend would just come in and ruin all of that. A boyfriend would probably want to hang out with him and Aerith. No. No way. He didn’t want that.

* * *

Zack wasn’t always the smooth talking, suave, sexy man he was today. No. Not at all. Far from it. He had horrible experiences in college. Sure, he had hookups, but he tended to get a little too attached, and would scare them away too soon.

So he had learned from his past mistakes, and wanted to pass on that knowledge. 

And if there was ever a man who needed education, it was Wedge Kusabi.

Wedge worked as a tax consultant. His colleagues would consider him goofy, awkward, and a total klutz. His colleagues weren’t wrong, per say, but they weren’t totally right, either. They never took the chance to actually get to know the man. In fact, Wedge was kind, funny, optimistic, thoughtful, and friendly. He was also the type of person in a friend group, that would make sure everyone was included. The man truly had a heart of gold.

Zack’s business was only referable, in order to stay under the radar, and so no one would ever figure out who he was. If they did? Well, Zack didn’t want to think about it. He’d also met in public places. A park, outside a coffee shop, a crowded restaurant, or, in Wedge’s case, the steps of the New York Public library at 1 pm on a Tuesday.

Zack couldn’t help but laugh as he watched the man who had requested his help. Wedge was eating a hotdog, with all the fillings, took one bite, and the mustard and relish slipped onto his pants. Wedge freaked out and tried to clean his pants up, only to spread the mess even further. He sighed in defeat and scooted over on the steps a little. Shaking his head, he approached the man.

“Is it safe to assume she’s single?” Zack greeted, stomping down some steps so he was sitting down next to Wedge.

“Yeah. Yeah of course. But she’s way, _way_ out of my league bro. Is that going to be a problem?” Wedge looked over to him, already feeling like he failed.

“No. I’ve had some difficult clients, and haven’t failed any of them yet!” Zack beamed, taking a seat next to him. “So what’s her name?” Zack asked.

“Jessie Rasberry.” Wedge replied, whispering as if it were a secret.

“The Broadway actor?” Zack’s eyes went wide in shock. Who did Wedge think he was kidding? “From the play Loveless?” Zack had expected the woman Wedge was pining for was going to be a difficult catch, but he didn’t expect a famous actress. 

“Yeah, that’s her! Crazy, right?” Wedge laughed awkwardly, looking down at his feet, as if he were ashamed. 

“Isn’t she dating her co-star, Genesis Rhapsodis?” That’s the last rumor he heard, didn’t even know if it were true or not.

“Nah, didn’t you see the articles about Genesis making out with some guy on a beach in the Bahamas? The Daily Moogler released the article yesterday. It was crazy, bro.”

Zack really wasn’t into the gossip scene. So no, he didn’t hear about it. He had heard of the Moogler, though. It was probably the most popular gossip site on the internet. A lot of other articles quoted it. Typically, if there was drama or breaking news, the Daily Moogler had announced it first.

“Do you know her personally…or….?” Zack trailed off. All of his clients _knew_ whoever they were pining after. Even if it was just a co-worker, or a classmate, and even if they hadn’t actually spoken to them yet. They still knew them. If Wedge didn’t know Jessie, well, that would make it a lot more difficult. Almost impossible, even.

“Yeah, of course! I’m one of her tax consultants.” 

“Does she know you’re interested?”

“No...No she doesn’t.” Zack sighed. Okay, maybe this was going to be a little more difficult than he thought.

“Does she know your name?” Zack asked. Surely, she had to know something about Wedge, right?

“Nah, there’s so many of us there. I wouldn’t expect her to remember.”

“Does she know you exist?” 

“Uh…” Wedge trailed off, and Zack sighed. Alright, this’ll definitely be way harder than anticipated.

“I know it’s crazy isn’t it? Okay. I get it. I just figured with your help it might…” Wedge stood up, dusting off his pants, as if doing so would rid the stain the mustard had caused. When Zack didn’t answer, Wedge continued, feeling suddenly defeated. 

“Guess you’ve never felt so hopeless before? Like you’ve never loved someone so much it breaks your heart to think she wakes up every morning with the wrong man? I’m sorry I wasted your time, okay? Never mind.”

“Hold on, Wedge. I’ll help you. This isn’t going to be easy, but I’ll help you.”

“Really?! Oh wow! Thanks, bro!” Wedge leaped forward a little, hugging Zack around his waist. Zack squirmed a little in the hold, but allowed the other man to hug him.

“Alright Wedge, happy to help. My name is Zack Fair, by the way. And I’ll help you get your dream girl.”

Zack knew he was in for a rough time. The last guy Jessie had dated basically owned ShinRa electric company. Or was the heir, or something of the sort. The only saving grace was that she was a celebrity, so her life was out in the open. Some quick Google searches taught Zack everything he needed to know about her, and about how he could help Wedge woo her.

* * *

Zack had been going to the same bar, almost every night, for the last three years.

But he never saw _him_.

Blond spikey hair, pretty blue eyes that were practically shining through in the darkness of the bar. Gorgeous arms, too. He looked like he worked out, judging by the muscle attoning his arms. He also looked small, petite, even. Which was perfect, because he had a thing for smaller men Especially when said man could handle himself well. And with the scowl this guy was sporting, he could most definitely handle himself.

He seemed distracted, kept looking at his phone, then looking up, eyes at the entrance. Waiting for someone, maybe? He watched the blond for a while, watched as he completely ignored any hot woman that passed him by. Didn’t even give them a small glance. Didn’t look up from his phone. That told Zack that blondie didn’t seem interested in women.s

But what Zack did notice was that blondie was looking at him, when he thought Zack was looking away. He could practically feel those gorgeous blue eyes taking him in. It made him shiver, to the point where he could feel the hairs on his neck stand up, feeling blondie’s eyes on him. 

“He comes here a lot. Works for some sort of online gossip site. Great tipper. Really quiet though. Seems a bit standoffish, but he’s cordial and kind to the bartenders. Sometimes he’ll meet up with two women, but I think one of them is his sister.” The bartender explained, must have realized Zack had been staring for the better part of an hour.

“What’s his drink?”

“He usually drinks beer,” The bartender shrugged. “Tonight he’s having a martini on the rocks. Maybe he had a hard day or something.”

Zack began walking over, two drinks in his hand, but the moment he approached the blond, another man, a red-head, suddenly approached him, also a drink in hand. Zack turned his back to them, listening in. Something told him that his red-head was going to strike out. Then he’d swoop in.

“Noticed you were almost empty, so I brought ya another.” The red-head sat on the chair across from the blond, placing the drink on the table between them, and sliding it over to Cloud, slowly.

“Thanks,” Cloud said. Great. Another annoying man that was probably going to ask him on a date. Sure, he liked men, was gay, but did he have “I am gay” written across his forehead? Why did men always approach him? Especially when he wanted to be left alone. 

“Can’t help but think you look like my next boyfriend.” Cloud had to hold back from rolling his eyes into the back of his head. Fuck that was a terrible pick-up line. How could anyone ever think that was a good opener? Who in their right mind would fall for that one? 

“Not interested.” 

“You got pretty eyes. I’m Reno, by the way. What’s your name?” The redhead pressed, clearly not reading Cloud well enough.

“Can’t take the hint?” Cloud sighed. Shit. Why were men like this to him? This is why he avoided any hint of a relationship.

“You always this standoffish and shut-off? How are you ever gonna find a man if you don’t let any in or even talk to you? Are you so afraid that the right man will sweep you off your feet?”

Zack cut in speaking over Reno at the same time “-sweep you off your feet?” 

Reno looked up Zack, shocked.

“Sorry I’m late babe, Uber took forever and was surging. Work was good?” Zack asked, looking into the blond's eyes. If he read him correctly, he would-

“It was fine. Boring, but fine.” Blondie shrugged, both men looking at Reno.

“Nice to meet you, Reno.”

Reno huffed, clearly annoyed at Zack, but didn’t want to deal with him just to get with Cloud. He left the drink he had bought for Cloud and left with a dramatic sigh.

“Must be annoying, yeah?” The voice pulled Cloud out of his angry thoughts, turning to the handsome man that had taken Reno’s seat. He was handsome, Cloud wouldn’t deny that, but what did he want? To hit on him, just like every other man out there? How did they even know he was into other men? Got annoying, at times.

“Sure,” He shrugged, taking a sip of his drink, doing the best to ignore the man who was talking to him. Sometimes it worked. They’d just get bored or annoyed and walk away.

“I bet you’re wondering why they all approach you? ‘Cause you must be thinking ‘Do I have ‘I’m into men’ plastered on my forehead?’. Which no, you don’t. A lot of men just come here and hit on the first thing that moves. Gross, really.” Cloud raised an eyebrow. The hell was this man going on about?

“Guess so,”

“But you? You haven’t even looked at a single woman that passed by you tonight. That’s what gave it away to me, at least.”

“Hmm, been watching me?” Cloud asked, not even sure if he liked the idea or not. No way he’d tell this guy that he was actually watching _him_. Had his eyes on him all night. Couldn’t help it.

“Wouldn’t you like to know,” There was a teasing tone to his voice, a smirk, and Cloud almost wanted to punch the smug look off this guy’s face. But there was also something almost safe about his demeanor. 

“But,” The man continued. “Out of all the people that have been in and out of this bar, the only person you’ve noticed today, has been _me_ ,” Cloud gasped, turning away to conceal his blush. Had this man really noticed he was watching him? Cloud swore he was being sly about it. Made sure he was watching while this guy was turned away. Their eyes hadn’t met once.

“But yeah, must be hard when you just wanna be left alone. Maybe one guy will pique your interest, introduce himself and say; hi, I’m Zack Fair and I’m a consultant. And you’ll say...?” The question lingered, and Cloud had inner turmoil. He always ignored those men, or asked them to leave. But this guy seemed... different.

“I’m Cloud Strife, and I work the gossip column for the Daily Moogler.” Cloud loved his job, absolutely loved it. But he hated telling people where he worked, unless he got to know them first. Too much judgment from others.

“Then what would the guy do? Fake interest? To get me in bed or something? Sounds suspicious.” Cloud asked, eye raised in curiosity. Maybe this guy, Zack Fair, really was like any other annoying guy that tried to hit on him when he really just wanted to be left alone.

“No,” Zack laughed, leaning forward a little. “He’d be very interested. But then he’d realize that he’d never have a chance with someone as handsome as Cloud Strife.”

“Hmm, then what?” 

“Then we’d both move on. Live our lives. And I think we’d both be just fine.” Zack stood up, smiling down at Cloud. Cloud could see a scar on Zack’s chin. Hmm, didn’t notice that before.

“Nice to meet you, Cloud Strife. Just don’t let those assholes get to you, yeah?” The man said, walking away, not turning back, not even giving Cloud a chance to reply.

“Hey, this is for you,” A bartender handed him a drink. The same one he had been drinking. “From the man that just left.”

Cloud sat up, eyes wide, searching for the dark-haired man who just left. How did he even…?

“Wow Cloud, thank you. You got me a drink, what a great friend.” He was so preoccupied with Zack, that he hadn’t even noticed Aerith come in and sit down next to him.

“You okay?” 

“Uhh, yeah.”

* * *

“I feel bad for her sometimes.” Wedge explained. He and Zack are sitting at a local coffee shop. Their first meeting since they had first met, a few days ago.

“How so?” Zack always prided himself on giving his clients his full and undivided attention, but he’d be lying if he said he wasn’t at least a little distracted, thinking of his and Cloud’s upcoming date.

“All her other consultants don’t like to let her use her own money! Bro, she wanted to invest in a company, and they suggested against it, she got so discouraged that it hurt me!”

“Hmm, did you speak up?”

“Me? Nah bro, of course not. My coworkers barely notice me, I can’t imagine any of them would let me speak up.”

“Alright, so next time it happens, do it.”

“Wait! Come on, I can’t just...do that!”

“Why not?”

“They’ll...speak above me.”

“Well, can’t know until you try!”

Except Wedge didn’t know how to try. He hadn’t worked there as long as his coworkers, who were all middle aged me. He was by far the youngest, and least experienced. So it was hard for anyone to just take him seriously.

“My friend Biggs is opening an art school for underprivileged kids. I wanted to help by donating $500,000 to get him started.” Jessie smiled, leaning forward on her hands, watching for the reactions.

“I’m not so sure that’s a good idea. Too much money to get started.” The older man, Corneo said, not even meeting her eyes, while he scribbled down something in a notebook.

“Yes, better to invest your money somewhere instead, to make more money back.” Palmer agreed, also not even looking at her.

“Oh, I don’t care about the money,” Jessie spoke a little louder. “I just want to help my friend, and help the kids in the long run.”

“Perhaps next time.” Heidegger shrugged, also ignoring her.

She sighed. “Fine, fine.”

“I think it’s a great idea!” Wedge spoke up, his heart immediately pounding when his coworkers all turned to him, shocked, like they never expected him to speak. And honestly, it was very possible that some of them hadn’t.

“Excuse me?” Jessie blinked, surprised someone was standing up for her in this group. These men always seemed to agree with one another. If one of them said one thing, they’d all silently agree.

“I think you should donate as much as you want to your friend. It sounds like a great place to donate money to!” Wedge was looking at her, watching how her pretty brown eyes were slightly wide in shock, how her lips were upturned in a little smile. She was so beautiful and he wanted to just stare at her all day.

“Wedge, I don’t think that’s a good-” Palmer began, it took him a moment to even remember Wedge’s name.

“No!” Wedge yelled, causing the other men in the room to freeze. “It’s her money, let her do what she wants with it.”

“And we’re her tax consultants. So we’re here to give her advice on how to use her money.”

“Yeah, but like...advise her, not tell her what to do.”

“We’re not telling her-”

“But you are! Every time you tell her no! Let her do what she wants. You break her spirit a little bit each time you say no.” Wedge pounded his fists on the table, standing up in annoyance and anger. Had they always been this...horrible?

“Wedge Kusabi, if you don’t sit down-”

“I quit!” Wedge yelled, pushing back his chair and standing up, making his way to his office. Time seemed to almost slow down, as they all watched him leave, and almost trip over his own two feet. 

Once he made it back to his office, he started freaking out.

“What happened?” Zack was there, told him he’d be there for moral support. Seeing Wedge practically run in, slamming the door behind him was the last thing he had expected.

“I quit! I...I didn’t want to quit my job. I just wanted Jessie to notice me. I never wanted to quit. Oh no, I’m in too deep now aren’t I?” 

“Calm….calm down Wedge. It’s okay.”

“I quit my job, bro! What am I supposed to do now?” He was almost hyperventilating, holding his hand to his chest to try to calm him breathing.

“You can find another job just fine.” Zack said. Wedge honestly did seem very smart, and it was probably the best thing to happen to him. He deserved a job where his coworkers actually cared and paid attention to him.

“But what if I become homeless? What will I do? I have a cat! I can’t just-” There was a soft knock on the door, and both men slowly turned to the knock.

“Hello? Wedge? Are you in there? It’s me, Jessie.” Wedge’s eyes widened, turning to Zack, mouthing “What do I do now?”. Zack pat him on the back and slowly pushed him to the door, hiding just out of view

“See what she wants.” He said, motioning for him to open the door. Wedge looked at him with pity, almost like he was afraid. Taking a deep breath, Wedge opened the door, making sure he was standing completely in the doorway, so Jessie wouldn’t try to get in.

“Hi!” She greeted cheerfully, raising her hand and waving. Cute. Wedge thought. She was so cute.

“Say hello back,” Zack whispered.

“Oh, uh, hello.” Wedge muttered.

“So um, no one has ever stood up for me like that. Thank you.” She seemed so genuinely thankful. It made Wedge’s heart break, to hear that no one has stood up for her before.

“So I was wondering!” She sang, one finger up in the air, like she was going to ask a question. “Maybe you can be my own personal consultant?”

Wedge stood there awkwardly, for so long, that Jessie was getting concerned. 

“Umm, Wedge? You okay?” She leaned forward, almost ready to tap his nose, but Zack snapped his fingers, snapping Wedge out of whatever dimension he was in.

“Yeah, yeah! Sounds great.”

“Alright, well, can I give you my number? And maybe we can meet up on Wednesday?”

“Oh umm, Wednesday?” Wedge saw Zack out of the corner of his eye, nodding his head.

“Yeah? Sound good? We can figure out details. Gimme a pen and paper.” 

Zack reached for Wedge’s hand, hidden from Jessie, and handed him a pen and post-it note, Wedge slowly moved his hand, giving Jessie the pen and paper.

“Thanks!” She smiled, quickly scribbling down her number and handing it back to Wedge.

“Okay,” She laughed. “I’ll look forward to your call.” She tilted her head a little, gave Wedge a quick wave, and turned to leave. Wedge watched her until she got into the elevator. Zack slowly shut the door, and Wedge leaned up against it, letting himself slowly slide down to the floor.

* * *

“Cloud Strife?”A voice called out to him, one he had never heard before. Andrea led the young man to Cloud’s desk. He looked like he was some sort of delivery guy.

“Huh?” Cloud looked up from his lunch, blinking a few times in confusion. A delivery? For him? At work? That’s honestly never happened before.

“You’re Cloud Strife?” The man asked again.

“Yes?” Cloud answered like he was unsure if he should even answer.

“Alright, great. Sign here.” He handed Cloud an iPad to sign, which Cloud signed quickly, handing it back. The man handed him a box, which Cloud opened quickly pulling out a walkie talkie. He turned it around a few times and clicked it on, immediately, a voice came booming through.

“Sucks when a guy calls someone who doesn’t give them their number. So this is me, not calling you.” There was a gentle teasing tone in his voice, and by now, everyone in the office was watching. Andrea’s eyes were slightly wide, and Kunsel was looking on with interest. Vincent and Cid were watching too, feigning non interest, but watching none-the-less. 

“How is this any better?” Cloud asked, suddenly feeling like he was the center of attention. Something he hated more than getting hit on.

“Less invasive!” Zack joked.

“Uh-huh,” Cloud said slowly.

“So how about one date?”

There was an audible gasp throughout the room, and Cloud wished his glare could bounce off the walls and just hit everyone at once.

“A date?”

“Yeah, how about dinner Friday night?” Zack asked, hopefulness in his voice.

“Not interested.” 

“Alright, how about Sunday for lunch?” He asked again, still hopeful.

“I uh have a date?” Cloud lied. There was a collective eye roll in the room that he could practically hear. His coworkers were doing a shitty job at pretending they weren’t listening.

“You’re a difficult one, aren’t you Strife?” 

“Not really. And don’t call me Strife.”

“Why not?”

“Sounds too impersonal for someone asking me out on a date.”

“Oh? Okay. Cloud it is. Or Cloudy? Yeah, Cloudy!” There was a snickering of laughter throughout the office causing Cloud to roll his eyes again.

“So Saturday morning? For breakfast? Then I’ll take you out for some fun.” Zack asked, this time, sounding completely convinced that Cloud would say yes.

Cloud sighed, looking at everyone throughout the room. If looks could kill, his coworkers would have killed him ten times over. Also looked like they were egging him on, just begging him to say yes.

“Alright. Fine. Fine. Saturday morning it is.”

“Great! I knew you’d pick that! Dress warm and meet me in front of The Bad Waitress diner at 8am.”

“8 am? Zack, that’s so early I-”

“See ya then, Cloudy!” Radio silence. Zack was long gone.

“Alright, you said Saturday, right?” The delivery guy asked handing a box to Cloud. Cloud signed off and tore open the box. He pulled out a pair of snow goggles, a light green scarf, and some warm looking mittens.

“Uhh, what are these even for?” Cloud asked no one in particular, more so a question for himself.

“Maybe he’s taking you to an indoor ski slope? You enjoy snowboarding, right? Maybe he’ll take you snowboarding” Andrea offered. Yeah, that was true, there was some sort of mall that opened in New Jersey that has an indoor ski slope. 

“How would he know I can snowboard? He doesn’t know anything about me.”

“Well,” Loz said, “Best way to learn about each other is to go on a date!”

“Yeah, have fun Cloud. I can’t wait for you to tell us all about it.” Andrea said. Oh yeah, Cloud knew he’d be the happiest.

Cloud went back to his lunch, tuning out the chitter-chatter of his coworkers, all talking about him and his upcoming date.

Fuck.

What in the world has he gotten himself into?


	2. High on Love

**Summary for the Chapter:**

> Two dates? Wow, isn't Zack lucky?
> 
> Except he's not, because he messes it all up.

**Notes for the Chapter:**

> I am sooo sorry for taking forever! I had a rough and long October (and a rough November too I guess)! But now I'm back! So I hope you enjoy Zack messing up on his dates! And then Wedge and Jessie being cute together.
> 
> There are a few small references to NY and NJ things, but don't worry if you don't understand them. If you do, let me know haha. 
> 
> This is also mostly un-edited. But I'm tired and wanted to post the chapter. So I'll edit it in the morning!

Rufus Shinra.

Zack knew that name. Everyone in the tri-state area knew that name.

Rufus was heir to the Shinra electric company. It had a monopoly over all of New York City, and generally the tri-state area. Basically what everyone used as their electric source, given no other option, because the company pushed out all others.

But why did  _ he _ need help? Surely he’d be able to woo a woman easily enough? Every other week there was news all over the internet about him being with another woman. Vacationing all over the world.

“Hey, Rufus Shinra?” Zack greeted. Rufus was already waiting for him, suited up, in an expensive cafe a few blocks from his office building. Probably trying to be secretive? But really, how was he being secretive coming to an overpriced cafe?

“Nice to meet you, I’m Bob Johnson.” Zack lied. He almost always gave his real name, but there was something about Rufus that he didn’t trust, and his first instincts on people were usually correct.

“So what’s she like?” Straight into it, Zack decided. He had to make sure Rufus was being truthful, considering he had a knack for sleeping around. That, and if his intuition was correct, he didn’t want to be around this guy more than necessary. 

“Beautiful. The most beautiful woman I’ve ever met. Have you ever met someone, that you just can’t get out of your mind?” Rufus asked. Yeah, Zack could relate. He couldn’t stop thinking about Cloud. Even though he’d seen him once, for a few short minutes. Those eyes were just so mesmerizing. Wow. He couldn’t wait for their date. He just wanted to stare into Cloud’s eyes, get lost in them. Maybe even-

Wait. Rufus, right. Zack almost forgot he was working right now.

“Yeah? That deep in?” Alright, maybe this guy wasn’t so bad? He called her beautiful instead of hot. He had met up with too many men that just wanted to get laid, and they always started off with calling the person ‘hot’.

“You have no idea! I just think about her all the time. I met her when I was at Victoria’s Secret, buying pajamas for my mom-” Zack laughed, interrupting him.

“You mean you were buying something for another woman? And you happened to meet her there?” Zack raised a brow. Who was this guy trying to fool? Zack wasn’t stupid.

“Alright, fine. Yeah, I was. But this other woman is so much hotter. All I could think about is fucking her since I first laid eyes on her.”

“Wait,” Zack stopped him before he could go on. Alright, so yeah, Rufus Shinra was a pig. “That’s not what I do. I respect people. I don’t get them together to get laid.”

“Hmm, no? Would more money help move this along?” Rufus was already reaching for his wallet. Bold of him to think Zack could be paid off like that.

“No. No way, fuck off.” Zack stood up angrily, eyes narrowing when he felt Rufus grab his wrist and tug at him.

“You sure? A little extra money could be helpful, and I have a lot of it. So name your price, money isn’t the issue.”

“Don’t really care, just let it go and leave her alone.” Rufus’ grip tightened on his wrist as if trying to keep him there.

“And you better remove your hand, because whatever part of you that touches me, you’re not getting back.”

* * *

Cloud hated mornings.

Even back in college, he made sure to never schedule a class before 11 am.  _ Refused _ to. He would have never woken up on time, much less be able to concentrate if he did actually wake up.

But now, here he was, 8 AM, in New Jersey of all places, waiting for Zack Fair so they could have breakfast together. Then after that? He had no clue. He just hoped it wasn’t something stupid. Although Zack seemed overly excited for wherever he was taking him.

It was a nice change, honestly. To have someone seem so genuinely excited to go on a date with him.

Not that Cloud would ever admit that.

“Cloud!” An overly happy voice greeted him. Ah, right on time. At least there was that. For a moment he was worried Zack would be late and he got up early for nothing.

“Morning,” Cloud nearly groaned, raising his hand slightly in greeting.

“Aww, not a morning person, Cloudy?” Zack smirked, giving him a small, amused laugh.

“Why do you keep calling me that?” Cloudy? No one had ever called him that before. Not even when he was a kid.

“Eh, it’s kind of cute? Don’t you think?” Zack shrugged.

“Cute…?” Cloud trailed off, raising an eyebrow in judgement. Was it normal to call your date ‘cute’?

“Come on, let’s go in, I’m starving.” Zack tilted his head towards the diner, leading the way and attempting to hold the door open for Cloud. Instead, they had both grabbed the door handle at the same time, basically holding each other's hand. 

Zack gasped and pulled away, acting like his hand had been burnt.

“S...sorry.” He mumbled, not even sure why he was sorry. All he did was touch Cloud’s hand, on accident.

“You first,” Cloud said as he held the door open for Zack, following right behind him.

They had met at a little diner off the highway. Nothing fancy, it seemed, and New Jersey was riddled with diners, a little ridiculous, Cloud thought, but the food was actually really good.

“This isn’t the date, y’know. Well, okay, maybe it is, or at least part of it. But the real date is coming up!” Zack smiled, seemed so proud of himself.

“Where are we going?” Cloud asked, taking a bite of his breakfast sandwich.

“You’ll see! It’s a surprise,” Zack wiggled his eyebrows, half in excitement. “I bet you haven’t gone there yet, either.” Zack laughed as he took a sip of his coffee. Getting totally lost in Cloud’s eyes, his hands slipped and he dropped the cup, coffee and ice spilling all over his shirt, drenching through.

Cloud brought his hand to his mouth, stifling his laugh.

“Ahh, come on…” Zack was, understandably, embarrassed. All the years he’s worked getting people together, literally made it into his job, and he messes up on his own date. And not even the date, it was the pre-date!

“I think I have an extra shirt in the compartment box of my bike. I’m not sure it’ll fit you, though.” Cloud was sweet to offer, but Zack wasn’t so sure anything of Cloud’s would fit. Zack was built. Arms and chest a lot more muscular. Sure, Cloud seemed built himself, but he was a lot smaller in stature, petite, even.

“Yeah, sure. Can’t hurt.”

“It’s big on me, so maybe it’ll fit you okay?” Cloud opened up the little storage attached to his motorcycle, pulling out a black t-shirt, handing it to Zack.

“Thanks, also, it's extremely hot that you ride a motorcycle.” He said as he stripped himself of his dress shirt. Cloud took it from him, quickly folding it and placing it in his storage compartment.

“Alright, so maybe it’s a little small, but it works? Could be like a muscle shirt or something?” Zack laughed. “How do I look?” He held his arms out, presenting himself to Cloud.

Muscle shirt was right, but Cloud wasn’t complaining. Zack was practically bursting out of the shirt. The sleeves barely moving past his shoulders, showing the definition in his arms, muscles toned from years of working out. Showed off his abs, too, peeking out from the bottom of the shirt, looked more like a crop top than anything else. Crop top muscle shirt? Was that even a thing?

“Ridiculous.” Cloud blinked, eyes not leaving Zack’s chest.

“Aww Cloudy. So mean.” 

“So where are we going?” Cloud asked, deciding it was best to change the subject before Zack realized he was staring. 

“Hmm, let me drive and you’ll see.”

“Wait, you didn’t drive here?”

“Nope. Took an Uber.” Zack shrugged. He didn’t have a car, anyway. Didn’t need one, living in New York City. He also grew up in Brooklyn, so he basically took the bus or subway his entire life.

“I’m not letting you drive Fenrir,” Cloud said, gripping his helmet in defense.

“Fenrir?” Zack asked, raising an eyebrow in confusion.

“My bike.” 

“Oh, well it’s a surprise, so I gotta! Have an extra helmet?” 

Cloud never let anyone drive Fenrir. Not even his own sister. But he was giving into Zack’s gentle pushing. Not even pushing. Zack just asked and that was all Cloud needed to hear. What the hell was he getting into? No way he was falling for this guy so quickly. He was such a dork. A hot, adorable dork, but a dork nonetheless. 

“Fine,” He said as he grabbed his extra helmet, handing it to Zack. They got on Fenrir, Zack smiling at how close Cloud was. Alright. He could get used to this. Maybe Cloud would take him for a ride one day.

“Hold on tight!”

* * *

“What? Really Zack? An indoor ski slope?” Cloud wasn’t exactly impressed, but he wasn’t bored either. In all honesty, it was kind of cool. He had heard of this place, the indoor ski slope, inside of a giant mall located in New Jersey. It was supposed to open _ years _ ago.

Cloud really loved snowboarding, so in all honesty, he was actually a bit excited.

“Yeah, cool, right?”

“Sure, really cool.”

Cloud didn’t tell Zack, but he was basically a pro-snowboarder. He grew up in the mountains and would snowboard for fun, since most of the time, there really wasn’t anything else to do in his sleepy little town. But here Zack was, trying to teach him the basics of snowboarding when it seemed that he himself didn’t know too much about it.

“Keep your core centered and balanced, otherwise you’ll fall! But, well, I’ll be there to catch you if you do,” Zack explained, smiling as he watched Cloud turn a little on the slope. “Turn with your back foot, and lead with your right foot. Oh, and use your left foot for steering.”

“Thanks, Zack, but I actually already know how to snowboard. I’ve been doing it my whole life.” Cloud replied, moving slightly towards Zack, so he could hear him better.

“Oh,” Zack blinked, frowning and looking forward. Here he was, thinking he had such a great idea! But Cloud already knew how to snowboard.

At least Cloud seemed to be enjoying himself.

“Zack look out!” Cloud yelled out, and Zack looked over at him. What did he have to look out for? This was a fake slope, it wasn’t as if there were tree’s here that he could knock into.

But suddenly, he felt Cloud grab his wrist and pull him closer. It caused him to lose his balance and fell towards Cloud, landing directly on top of him and tumbling down the slope. He vaguely felt Cloud wrap his arms around him, placing his hand on his head, like he was protecting his fall? Sweet. Really sweet.

When they finally stopped moving, Zack could hear an audible crack from Cloud’s wrist, and then a groan of pain from the poor blond.

“Cloud? Cloud are you okay?”

Cloud sat up slowly, face completely pale and eyes glossy.

* * *

Immediately after they fell, one of the workers had come to check on Cloud, a little worried that he looked pale beyond belief. They had called in to have an ambulance take him (and Zack) to the hospital. 

His wrist was broken. Nothing terrible, luckily just a very minor fracture, but it had still hurt more than Cloud had ever thought. He had never broken a bone before and never wanted to do so again.

Poor Zack, though. He had panicked so much. Kept apologizing on the way to the hospital. In any other situation, Cloud would have probably been angry. Or annoyed. 

But right now, he actually felt bad for Zack.

“Zack, it’s okay. I don’t blame you.” Even though it honestly was all Zack’s fault - Cloud had pulled him to avoid hitting another person because Zack wasn’t paying attention - Cloud just couldn’t be mad at the grown man who was literally pouting in front of him.

“Thanks,”

“Huh? For what?” Zack asked, why in the world would Cloud be thanking him?

“For coming with me, and staying with me. I hate hospitals. Had a bad experience as a kid. So, I’m glad you stayed with me.” Zack smiled in response, the way his lips curved up was almost blinding. It made Cloud smile back. Somehow, only hanging out for a day with Zack, most of which was spent in the hospital, Cloud could feel the other man's contagious happiness.

“Yeah, ‘snow problem Cloudy.” Zack said, barely able to get the words out, before he burst out laughing at his own dumb pun.

Cloud rolled his eyes, but was trying his best to hide the little smile that was forming on his face.

“Okay, so I guess I’m  _ not _ going to give you my number…”

* * *

“Cloud! What happened to your wrist?!” No greeting, no ‘hi, how are you’. That was the first thing out of Aerith’s mouth when they met for lunch the day after Cloud’s date with Zack.

“Zack took me to that indoor ski slope, the one in New Jersey. He tried to teach me to snowboard. Long story short, he failed and that’s how I broke my wrist.”

“So this was all his fault?”

“Yeah.”

“Didn’t you say he also spilled coffee on himself?” 

“Oh yeah, he did.” Cloud had almost forgotten about that. How could he forget Zack wearing his shirt, and it basically looking like a muscle shirt?

“Sounds like he failed.” She giggled.

“He did. It was ridiculous.”

“But...you’re going to see him again?” Aerith asking, prodding, poking. She had known Cloud for years, and she knew him well enough to know he hated when men tried too hard with him. And Zack definitely seemed like he tried too hard. Tried so hard that he failed badly.

“Well, I gave him my phone number, and I have his so…” Cloud trailed off, taking a few bites from his frozen yogurt. He felt weird talking about his date, hell, just talking about Zack made him feel awkward. Even if it was with his best friend.

“So the guy failed horribly and you still want to see him?”

“Yeah, there’s something...different about him.” Cloud said. It was true, Zack seemed so genuine about everything he said 

“Cute, you have a crush. About time! I can’t wait to tell Tifa.”

“What? I do not. And you better not tell Tifa.”

* * *

“I can’t just  _ call  _ her. What if she picks up?” Wedge asked. They were at his apartment, Jessie’s number that was scribbled on a piece of paper, tight in his hand.

“No one picks up for a number they don’t know. Do you?” Zack asked. Wedge was definitely proven to be a more difficult client. He had such little confidence in himself, which, while Zack saw in a lot of his clients, Wedge was different. He exhumed such energy and excitement.

“Well...no…” 

“Alright call her. Leave a message saying you can’t make your appointment on Wednesday.”

“But I want to see her.”

“Yeah, but you have to make her want to come back.”

“Alright, alright.” Wedge sighed, typing in Jessie’s number and pressing ‘call’. After only one ring, she picked up, cheery voice greeting with “Hello?”. Wedge freaked out and hung up.

“She picked up! You said she wouldn’t pick up!” Wedge yelled towards Zack, looked down at his phone when he felt it vibrate. “And she’s calling again!”

“Okay, so pick up.” 

“What do I say?”

“Start with hello?” Zack offered, giving him a little laugh to try to calm him down.

“Hello? Yeah, this is Wedge. Did I just call? Uhh,” Wedge looked up at Zack, for questions. Zack nods his head.

“I did, yeah, but I realized I was busy.” He looked up at Zack, who was nodding his head, trying to get Wedge to keep the conversation going.

“So uh, Wednesday? I can’t make it? Yeah, I have a lot of...things to do.” Zack shook his head. Wedge seemed to be falling back into the awkwardness. He picked up the tickets he had, to the art gallery.

“So there’s this...thing I have tickets to. An art gallery on Saturday. Maybe you can bring your friend Biggs? Get ideas for his school?” 

“Alright, great! I’ll email you the details and see you then. Looking forward to it.”

The moment he hung up, Wedge did a little dance.

“Uh Wedge? I’d suggest against doing that when you’re there...”

“Do what? Dance? Come on bro, if it’s one thing I can do, it’s dance!”

* * *

“Hey Wedge! Thanks again for the tickets!” Jessie greeted him with a smile and a thumbs up.

“Y...yeah.” Wedge gave her a thumbs-up back. She laughed and bopped him on the forehead, causing him to blush throughout his whole body. Anything Jessie did just made him giddy. She was just so cute, and beautiful, and -

“Uh, earth to Wedge? You okay in there?” She giggled, gently tapping his forehead with her knuckles, like she was knocking on a door.

“Oh! Yeah, yeah. Sorry I’m here! Let’s go in?” He offered his arm, almost freezing up, but holding himself together, as he led her into the building. 

He noticed the insane amount of paparazzi around, taking pictures, and calling her name. But to Wedge’s surprise, she was ignoring them, focusing her attention all on him.

“So where’s Biggs?” He asked as they entered the building.

“Late,” She rolled her eyes, but kept the playful smile on her face. “As usually. But don’t worry,” She sang. “He’ll be here!”

“Jessie, that you?” A man with short silver hair greeted her, followed by another man with silver hair. Wow, how many people had silver hair nowadays?

“Oh, yeah hi!” She greeted them each with a kiss to the cheek.

“This is Wedge!” She introduced him right away. Wedge held his hand out to shake their hands.

“This is Yazoo,” The man with the long hair shook his hand. “And Loz.” The other man, with short hair shook his hand.

“How have you two been?” She asked, seemingly just trying to make small talk. Wedge could already tell she didn’t want to be near them.

“Have you been to that new Thai restaurant in midtown?” Yazoo asked.

“Oh, not yet, but I-” 

“It’s disgusting.” He cut her off, turning to his friend as they laughed together.

Wedge could tell Jessie was annoyed, hurt, even, but she kept her chipper demeanor. 

“Did you hear of that new pizza place in downtown?” Kadaj asked.

“I have! My cousin and I went to it and-” 

“It’s disgusting.” He laughed together with Yazoo, the two seemingly sharing some sort of combined brain cell.

“What is your name, Lozenge?” Wedge asked, turning to Loz, who frowned at the mispronunciation of his name.

“It’s Loz.” He corrected, clearly not picking up that Wedge had done it on purpose.

“What do you think of the new mall in the Meadowlands? The one that finally opened after years and years?”

“Uhhh…?” He trailed off, dumbfounded at what Wedge was asking him.

“Let me guess, disgusting?” He asked, and Jessie laughed into her drink, obviously appreciating that he had stuck up for her, and enjoying the way he did it.

“Nice to meet you.” He said to them as he led Jessie away. She gave them a little wave and a shrug, scooting closer to Wedge as they left them confused at what had happened.

“Thanks, I actually can’t stand them. I worked with them on an episode of a show that I guest-starred in. I usually avoid their calls. Loz is kinda dumb, anyway. But they’re both so annoying.”

“Yeah? I dunno, I kind of like them.” Wedge smiled.

After another half an hour, Wedge saw a man approach Jessie, give her a hug, and then look over to him. Wedge straightened up, remembering what Zack had said to him.

_ “Remember that tonight isn’t about yourself, or even getting closer to Jessie. Tonight is all about Biggs. So make sure you actually listen and respond.”  _

_ “All about him, right.” _

“What made you want to open up an art school?” Wedge asked.

“I love kids, honestly. I was an orphan, and grew up in an orphanage. I just always felt the need to kinda pay it forward. And it makes me happy, seeing the kids happy. I want people to realize how much the arts can help kids.”

“That’s great, bro! I was an orphan too, actually.” 

“Oh, you were?” Jessie piped up, suddenly feeling a little sad. She had such wonderful parents, a great childhood, but here were two great men, who turned out amazing, without parents.

“Yeah, my parents died when I was young. Too young to remember them.” Wedge explained, no sense of sadness apparent on his face.

“Same here, but it seems like we both made our way in the world.” 

“Yeah,” Wedge agreed. He was always proud of his accomplishments, having done them all by himself. 

Then he remembered what Zack had said to him, about not getting too personal during this date.

“So...drinks? I’ll get us drinks! Be right back.” Wedge said, awkwardly turning around and almost tripping, and then laughing at himself before making his way over to the bar.

“So this is the guy who quit his job because he stuck up for you?” Biggs asked.

“Yeah,” Jessie sighed, laughing as the duo watched Biggs order some drinks.

“Well, I like him.”

“Yeah, I do too.”

About an hour later, Biggs said his goodbyes and thanked Wedge for the tickets, getting his number before leaving.

And then Wedge found himself on the rooftop, dancing with Jessie. As excited as he was, he couldn’t help but find himself...bored. Just moving his arms a little, while Jessie was dancing all silly. Deciding to forget about what Zack said for just a little while, and started dancing silly with Jessie, putting a smile on her face, as well as his. 

Yeah, this was way more fun, and Jessie seemed to be enjoying herself now.

The night came to an end all too soon, and Wedge was handing Jessie her jacket.

“So, do you like the Jets?” She asked, smiling as she took her jacket from him.

“Uhh, when they’re good?”

“So...that’s a no?” Wedge laughed, okay, fair. The Jets sucked and barely ever won games.

“I’m more into basketball than anything else. Plus, live games are like, so much cooler!” Wedge explained, realizing he had dropped most of his ‘serious guy’ act and was speaking more like himself. Oh no, would Jessie-

“Oh? So the Knicks?” Jessie giggled, letting him lead her out of the building, his arm wrapped gently around her waist, finally having gained the courage.

* * *

“Really Cloud? Weren’t you supposed to be there? What happened?” As soon as Cloud walked into the office on Monday, Kunsel was practically shoving his phone in Cloud’s face. Cloud pushed him away and took the phone, reading the article.

It was about Jessie Rasberry, the Broadway actor, seemingly on a date with some  _ nobody _ .

“Who is this?” Cloud asked. This guy definitely wasn’t an actor. Not even a wannabe youtuber or tiktoker. He was definitely a nobody.

“Sources say his name is Wedge Kusabi. No idea who he is.”

“They look...happy?” Cloud offered. Truly, they did. He always remembered seeing pictures of Jessie online, and while she smiled, her smiles never really looked genuine. But here, in this picture with Wedge? She looked so happy.

“Okay, but you were supposed to be there. What happened?” Kunsel asked, not really caring whether or not Jessie Rasberry, one of the biggest Broadway actors, was happy.

“I broke my wrist.” He replied, showing his bandaged wrist to his boss.

“Oh, on your date? With  _ Zack _ ? Zack Fair?”

“How do you...know his last name?”

“The original tickets didn’t belong to Wedge or Jessie. They belonged to someone named Zack Fair.” The tiniest gasp, barely noticeable, but Kunsel was able to pick up the shock present on Cloud’s face.

“Oh.”

“Yeah. Seems like your boyfriend gave them the tickets.”

“He’s not my boyfriend. We had one date.” Cloud replied, trying his best to defend himself, but Kunsel was having none of it.

“So maybe we can set up a double date? Ask him some questions?”

“What questions could you even have for him? And who says I even want to go on a second date?” 

“The way you were smiling when you came in today? I think you do.” Kunsel teased.

“So how about it? I won’t poke too much. I just wanna know how he knows Wedge, and who Wedge even is. How about a double date for laser tag? Cissnei got tickets for Friday night. Sound fun?”

“Fine.”

* * *

“Really? You think this is smooth?” Zack asked, voice not angry but full of amusement.

“Well she seemed like she had fun! She invited me to a Knicks game next week.”

“She invited…? That’s great Wedge!” 

“Y...yeah. I did that all on my own, bro! I can’t wait.”

“Alright, well, then let's talk about kissing.”

“Kissing?”

“Yeah, second date? Pretty sure she’ll wanna kiss you.”

“Okay, sure sure. Kissing. Yeah, I like kissing.”

“The first kiss is important. Eight out of ten people believe the first kiss will tell them everything they need to know about a relationship.”

“So do I just...go for it?”

“No. Read her first, see if she wants to. If she does, you’ll know. She’ll give you a sign.”

“A sign? Like what?” 

“She’ll play with her keys, before even trying to put them in the door.”

“And?”

“And then you kiss her. She’ll probably lean into you, stopping before her lips meet yours. And that’s where you close the gap and kiss her.” Zack explained, smiling at the text that Cloud had sent him. Cloud was complaining about a coworker, and how he always seemed to pry into his love life. 

“You think she’ll really want to kiss me?” Wedge asked, going all starry-eyed, just from thinking about it.

“Yeah Wedge,” Looking up from his phone to meet Wedge’s hopeful eyes. “I think she would.”

* * *

Zack nearly dropped his phone when he saw that Cloud was calling him. They had been texting back and forth a bit, flirting too (at least that’s what Zack told himself), but he never expected Cloud to  _ call _ him.

“He...hello?” He greeted, flinching to himself when he heard his voice crack. Damn, why was he so nervous?

“Hi Zack,” Cloud greeted back. “My boss and his girlfriend Cissnei have some tickets for laser tag on Saturday, wanna be my date?” Zack nearly threw up at the question. Cloud Strife, beautiful Cloud Strife was asking  _ him _ out on a date? Sure, it was a double date, but still! It was like heaven was shining down on him or something.

“Yeah, I’d love that Cloudy. Give me a time and a place, and I’ll be there!”

* * *

“So you’re the infamous Zack? The one Cloud won’t shut up about?” That was how Kunsel had greeted Zack. No ‘Hi, nice to meet you.’ Nope, just straight to teasing Cloud out in the open.

Cloud sighed. “Come on, Kunsel.” He shook his head, pulling Zack away from his boss. 

“Cloud...talks about me?” Zack asked, honestly surprised that Cloud had spoken to others about him, even after the shitty first date they had together.

“All the time.” Cissnei smiled. She knew Cloud well enough to know he never gushed about a man. So this was definitely a first. Not that he gushed about Zack. But Cloud had his own unique way of talking about someone he liked.

“So what do you do for a living, Zack?” Kunsel asked as they waited in line to get into their room. There were a few other people waiting with them, looking like they’d have a full team. Nice!

“I’m a consultant. Nothing fun or fancy, but it pays the bills.” Zack explained, stretching his arms out and pulling Cloud closer to him. Not really meaning to do it. He hadn’t even realized how close Cloud was to him. He made a little gasp and turned to Cloud, who was staring back, but then leaned into the touch.

It took them a few minutes until they were able to get in. They were suited up and shooting lasers around within minutes, Zack doing his best to impress Cloud, but Cloud had already tagged out two people on the opposite team.

He always told his clients they had to impress their dates, so it would leave a lasting impression, leaving them wanting more. Yet here he was, utterly failing, for the second time. He had to do something in order to tag at least one person out.

Noticing there was a short wall and hearing someone behind it, he decided to attempt to climb over it.

“Zack? What are you doing?”

There was a loud buzzing sound, and an announcement for Zack to come to the entrance. Cloud went with him, and much to Zack’s disappointment, he was being kicked out for climbing the wall. Apparently, that was in the papers they signed. Cloud, not wanting him to go alone, left with him. 

“Sorry Cloud,” He apologized as the two walked close together on the edge of Central Park. Sighing, Zack kicked a rock. It bounced off the root of a tree and bounced up, knocking into something.

“Ouch!” Zack whined, slapping at his neck moments later, realizing he had gotten stung by a wasp.

“You good?” Cloud asked.

“Uh, well, I’m allergic to wasps.” Zack could already feel his eyes getting watery and neck swelling up around the sting.”

“Wait, really? Come on, there’s a CVS around the corner.” Cloud said as he took Zack’s hand in his own, leading him towards the drug store, wanting to get some benadryl as soon as possible.

“C’mon Cloudy. I’m oky, r’lly.” His words were slurred, and in the light of the store, Cloud’s eyes widened, seeing the state that Zack’s face was in.

“Alright, come on, Benadryl. Lot’s of it.” Cloud led him to the aisle, grabbing the extra strength and bringing it to the register.

“Oh, whoa. Is he okay?” The cashier asked, looking at Zack with wide eyes as he rang up the medicine.

“Whadya mean? M’fine.” Zack slurred, catching his reflection in the mirror near the register.

“Wh...what? Tha’s me? Cloudy, le’s go ple’se.” Zack was panicking now, seeing exactly how bad he looked. His left eye was swollen shut, and his lip looked busted. How could Cloud bare to even look at him like this?

“Yes, yes we’re going.” With a quick ‘thanks’ to the cashier, they left.

Cloud decided to cut through Central Park, being the easiest and quickest route back to his apartment.

“Mmm, have I ever told you how beautiful you are, Cloud?”

“Yes, yes you have.” Cloud tightened the hold on Zack’s waist, holding him in place as they walked towards Cloud’s apartment. He almost thought about taking Zack home to his own apartment, but then he felt bad just...leaving him there. It was a little bit of a struggle, trying to get his keys while Zack had all his weight on him, but he managed to open his door and gently drop Zack on the couch.

“Mm, it’s nice here, beautiful.” 

“Thanks,” Cloud said, bringing him water. He brought a blanket, tucking the other man in. Wait. Was Zack calling his apartment beautiful, or him again?

“You’re really sweet, you know?”

“I guess.” Cloud shrugged, sitting on the end of the couch, propping a pillow behind him, and getting comfortable.

“Did you get teased a lot as a kid?” Zack asked softly, the effects of the Benadryl making him drowsy.

“What?”

“Sorry to pry, you don’t have to say anything.”

“It’s fine, I’m just surprised you asked. Yeah, I got bullied a lot.” He didn’t really talk about it. Not anymore. It didn’t matter. It was in the past, back when he was in high school.

“I’m sorry. Someone as sweet as you, you seem to care a lot about others, even if you try to hide it. I assume people took advantage of that?”

Wow, to say Cloud was shocked would be an understatement. No one really wanted to get to know him, and no one was even able to figure him out. But Zack? After two dates? Had him nailed down pretty well.

“I got into fights a lot as a kid.” Zack started.

“Someone I don’t doubt that,” Cloud smiled, watching as Zack got more comfortable, pulling the blanket up to his chest.

“Yeah, I hated when others got bullied. So I would get into fights with bullies, wait-” Zack paused. “Does that make me a bully?” 

“No Zack, I don’t think that makes you a bully. Maybe...a hero? In your own way?”

“I just,” He yawned, the medicine clearly hitting him hard. “Hated when amazing people like you got bullied. And wow? You think I’m a hero?”

“Maybe you were someone’s hero.”

Cloud didn’t even remember when he fell asleep. He remembered talking to Zack for a little longer, and then nothing. Had he really fallen asleep on the couch with Zack right next to him? 

Sitting up in shock, Cloud realized that Zack was gone from his spot of the couch. Blanket folded up neatly where he had laid last night.

Fuck, of course he messed it up. Zack probably thought he was pathetic, getting bullied as a kid, so he probably left the moment he was able.

Sitting up a little more, he realized his kitchen was an absolute mess. He could see dishes and soiled food everywhere. When did that even happen? Was that all Zack?

Where was Zack anyway?

As if on cue, the door opened, showing Zack with a paper bag and two coffees.

“Hey, uh,” He greeted, face a little red in embarrassment as he walked over to Cloud, taking a seat next to him on the couch. “I tried making breakfast, but couldn’t decide what to make you, so I wanted to make everything, but everything got burnt because I tried to make everything at once,” Zack explained, gazing at the mess in the kitchen.

“I see.” Cloud actually felt a little better now. Annoyed that his nice, clean kitchen was a mess, but still felt better than Zack didn’t just...leave.

“I’ll clean it up,” Zack placed the bag and coffee down. “After we eat!”

* * *

“Thanks, Cloud, for taking care of me.” Zack smiled, looking into Cloud's eyes. His pretty blue eyes. Fuck, he could get lost in them. Glancing down briefly, he realized Cloud was fidgeting with his phone.

“It’s fine,” Cloud shrugged, taking a step forward so they were practically touching.

“Maybe a third date?” Zack asked, leaning in and tilting his head downwards, watching as Cloud closed his eyes, tilting his head up.

Zack leaned in the final inch, capturing Cloud’s soft lips against his own. His hand going to the back of Cloud’s neck, gently rubbing his fingers against the soft skin and baby hairs. Cloud gasped a little, letting Zack slip his tongue into the kiss. Too short of a kiss, Zack thought when Cloud pulled away.

Cloud smiled as he took Zack’s face in his hand, gently rubbing his thumb across the scar on his lower cheek and leaning in for a quick peck on the lips.

“Yeah, maybe.” He said as he walked away. 

Zack’s eyes went wide, watching, for a few seconds as Cloud walked away. He took a deep breath and turned heel, promptly tripping on his own two feet and falling to the ground. He looked over to see Cloud smiling and rolling his eyes before walking away, giving him a little wave.

**Notes for the Chapter:**

> Hope you all liked this chapter! I should be getting out some new chapters of my other fics soon! I'm also going to write a series of Christmas stories! Some sweet and fluffy one-shots. So look out for those if you want fluff (smut too!). Thanks for reading!

**Author's Note:**

> So I know I wanted to finish my other two WIPs before I posted another fic, but I've been so inspired and have basically written this whole fic. My plan was to post two different fics first, but this one kept bothering me haha. So I hope you enjoy!  
> Also, Zack seemed really smooth in this chapter, but just wait until they have their date.


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